EP0080602A1 - Substituierte Benzimidazole, Verfahren zu ihrer Herstellung, ihre Anwendung und sie enthaltende Arzneimittel - Google Patents
Substituierte Benzimidazole, Verfahren zu ihrer Herstellung, ihre Anwendung und sie enthaltende Arzneimittel Download PDFInfo
- Publication number
- EP0080602A1 EP0080602A1 EP82110054A EP82110054A EP0080602A1 EP 0080602 A1 EP0080602 A1 EP 0080602A1 EP 82110054 A EP82110054 A EP 82110054A EP 82110054 A EP82110054 A EP 82110054A EP 0080602 A1 EP0080602 A1 EP 0080602A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- methoxy
- benzimidazole
- trifluoromethyl
- pyridylmethyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 0 CC1C=*C(C=*)=C(C)C1C Chemical compound CC1C=*C(C=*)=C(C)C1C 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the invention relates to new substituted benzimidazoles, processes for their preparation, their use and medicaments containing them.
- the compounds according to the invention are used in the pharmaceutical industry as intermediates and for the manufacture of medicaments.
- German Offenlegungsschrift DE-OS 18 04 450 describes benzazole derivatives which are said to have tuberculostatic, insecticidal, fungicidal, antiviral, anthelmintic and anti-inflammatory activity.
- 2-benzimidazolyl-2-pyridyl sulfides are claimed, some of which are said to have a gastric acid secretion-inhibiting and some to have a gastric acid secretion-stimulating effect.
- - In DE-OS 25 48 340 2-benzimidazolyl-2-pyridyl sulfoxides are described which stimulate the exogenous or endogenous gastric acid. should inhibit secretion.
- EP-B1 0 005 129 also describes 2-benzimidazolyl-2 pyridyl sulfoxides, which are to be used in pharmaceutical preparations for inhibiting gastric acid secretion.
- the correspondingly substituted sulfides which can be used for the preparation of the above-mentioned sulfoxides are described in DE-OS 25 48 340 and in EP-B1 0 005 129 exclusively as an intermediate without indication of a pharmacological activity. -
- EP-A1 0 045 200 describes substituted heterocyclylalkylsulfinylbenzimidazoles which are to be used in combating or preventing certain gastrointestinal inflammatory diseases.
- Suitable salts for compounds of the formula I in which n is 0 are all acid addition salts. Particular mention should be made of the pharmacologically acceptable salts of the inorganic and organic acids commonly used in galenics. Pharmacologically incompatible salts, which may initially be obtained as process products in the preparation of the compounds according to the invention on an industrial scale, are converted into pharmacologically acceptable salts by processes known to the person skilled in the art.
- Suitable as such are, for example, water-soluble and water-insoluble acid addition salts, such as the hydrochloride, hydrobromide, hydroiodide, phosphate, nitrate, sulfate, acetate, citrate, gluconate, benzoate, hibenzate [2- (4-hydroxybenzoyl) benzoate], fendizoate (O- [ (2'-hydroxy-4-biphenylyl) carbonyl] benzoate), butyrate, Sulfosalicylate, maleate, laurate, malate, fumarate, succinate, oxalate, tartrate, amsonate (4,4'-diaminostilbene-2,2'-disulfonate), embonate [4,4'-methylene-bis- (3-hydroxy-2 -naphthoate)], metembonate [4,4'-methylene-bis- (3-methoxy-2-naphthoate)], stearate, tosilate (p-
- the above-mentioned acid addition salts can also be prepared from compounds of the formula I in which n is 1 (sulfoxides), but these do not have the same stability in aqueous solution as the salts of the sulfides.
- basic salts of the sulfoxides can be prepared by reaction with suitable deprotonating agents (e.g. inorganic or organic bases), which are also the subject of the invention.
- the invention further relates to a process for the preparation of the substituted benzimidazoles of the formula I, in which R 1 , R 2 and n have the meaning given above, and their salts.
- a suitable leaving group Y is, for example, a group which, together with the sulfinyl group to which it is attached, forms a reactive sulfinic acid derivative.
- Suitable leaving groups Y are, for example, alkoxy, dialkylamino or alkyl mercapto groups.
- suitable leaving groups Z, Z 'or Z include halogen atoms, in particular chlorine atoms, or hydroxyl groups activated by esterification (for example with p-toluenesulfonic acid).
- a metal atom M ' is, for example, an alkali metal atom (Li, Na or K), or an alkaline earth metal atom (e.g. Mg) which is substituted by a halogen atom (e.g. Br, Grignard reagent), or any other optionally substituted metal atom, of which it is known that it reacts in substitution reactions of organometallic compounds such as the metals mentioned above.
- a metal atom M ' is, for example, an alkali metal atom (Li, Na or K), or an alkaline earth metal atom (e.g. Mg) which is substituted by a halogen atom (e.g. Br, Grignard reagent), or any other optionally substituted metal atom, of which it is known that it reacts in substitution reactions of organometallic compounds such as the metals mentioned above.
- a halogen atom e.g. Br, Grignard reagent
- the reaction of II with III is carried out in a manner known per se in suitable, preferably polar solvents (such as methanol, dimethyl sulfoxide, acetone, dimethylformamide or acetonitrile) with or without water. It is carried out, for example, in the presence of a proton acceptor.
- polar solvents such as methanol, dimethyl sulfoxide, acetone, dimethylformamide or acetonitrile
- a proton acceptor Alkali metal hydroxides are suitable as such, such as sodium hydroxide, alkali metal carbonates, such as potassium carbonate, or tertiary amines, such as pyridine, triethylamine or ethyldiisopropylamine.
- the reaction can also be carried out without a proton acceptor, with the acid addition salts initially being formed, depending on the nature of the starting compounds.
- the reaction temperature can be between 0 ° and 150 ° C, wherein temperatures between 50 ° C
- reaction of VI with VII is preferably carried out in polar, optionally water-containing solvents in the presence of a strong acid, e.g. Hydrochloric acid, especially at the boiling point of the solvent used.
- a strong acid e.g. Hydrochloric acid
- Suitable oxidizing agents are all reagents customarily used for the oxidation of sulfides, in particular peroxyacids, such as, for example, peroxyacetic acid, trifluoroperoxyacetic acid, 3,5-dinitroperoxybenzoic acid, peroxymaleic acid or preferably m-chloroperoxybenzoic acid.
- the reaction is advantageously carried out in inert solvents, for example aromatic or chlorinated hydrocarbons, such as benzene, toluene, dichloromethane or chloroform.
- the reaction temperature is (depending on the reactivity of the oxidizing agent and degree of dilution) between -70 0 C and the boiling point of the solvent used, but preferably between -30 ° C and + 20 ° C.
- Oxidation with halogens or with hypohalites for example with aqueous sodium hypochlorite solution, which is expediently carried out at temperatures between 0 ° and 30 ° C., has also proven to be very advantageous.
- the reaction of IX with X is preferably carried out in inert solvents, as are usually used for the reaction of enolate ions with alkylating agents.
- aromatic solvents such as benzene or toluene may be mentioned.
- the reaction temperature is (depending on the nature of the alkali metal atom M and the leaving group Z) generally between 0 ° and 120 ° C, the boiling point of the solvent used being preferred.
- M Li (lithium) and Z is Cl (chlorine) and the reaction is carried out in benzene]
- the boiling point of benzene 80 ° C is preferred.
- the compounds XI are reacted with the compounds XII in a manner known per se, as is known to the person skilled in the art for the reaction of organometallic compounds.
- the compounds according to the invention are initially obtained either as such or in the form of their salts.
- the salts are obtained by dissolving the free compounds in a suitable solvent, e.g. in a chlorinated hydrocarbon, such as methylene chloride or chloroform, or a low molecular weight aliphatic alcohol (ethanol, isopropanol), which contains the desired acid or base, or to which the desired acid or base - optionally in the precisely calculated stoichiometric amount - is then added .
- a chlorinated hydrocarbon such as methylene chloride or chloroform
- a low molecular weight aliphatic alcohol ethanol, isopropanol
- the salts are obtained by filtration, reprecipitation, precipitation or by evaporation of the solvent.
- Salts obtained can be alkalized or acidified, e.g. B. with aqueous sodium bicarbonate or with dilute hydrochloric acid, are converted into the free compounds, which in turn can be converted into the salts.
- the compounds can be purified in this way, or pharmacologically incompatible salts can be converted into pharmacologically acceptable salts.
- the sulfoxides according to the invention are optically active compounds.
- the invention therefore includes both the enantiomers and their mixtures and racemates.
- the enantiomers can be separated in a manner known per se (for example by preparing and separating corresponding diastereoisomeric compounds).
- the enantiomers can also be prepared by asymmetric synthesis, for example by reacting optically active pure compounds XI or diastereoisomerically pure compounds XI with compounds XII [see K.K. Andersen, Tetrahedron Lett., 93 (1962)].
- the compounds according to the invention are preferably synthesized by reacting II with III and, if appropriate, subsequent oxidation of the sulfide VIII formed.
- the compounds of the formulas II-VII and IX-XII are either known, or they can be prepared analogously according to known regulations.
- compounds II are obtained by reacting compounds VI [E. Pouterman et al. Girardet, Helvet. Chim. Acta'30, 107 (1947)] with carbon disulfide.
- the compounds III can according to O.E.Schulz u. S. Fedders, Arch. Pharm. (Weinheim) 310, 128-136 (1977).
- the compounds IX are obtained, for example, from the compounds II by methylation, oxidation and subsequent deprotonation - e.g. with alkali metal hydrides or - alcoholates or conventional organometallic compounds - obtained.
- the compounds X are prepared based on Z. Talik, Roczniki Chem. 35, 475 (1961).
- Mp Means melting point
- ether stands for diethyl ether
- ethyl acetate means ethyl acetate.
- the abbreviation h is used for hour (s) and min for minutes.
- Example 2 Analogously to Example 1, 0.1 g of the title compound, mp. 166 ° C. (with decomposition, recrystallized twice from isopropanol), starting from 0.3 g (0.92 mmol) of 5-trifluoromethyl-2 - [(4-methoxy 2-pyridylmethyl) thio] - (1H) -benzimidazole and 0.3 g of 85% m-chloroperbenzoic acid.
- Example 5 3.5 g of the title compound with a melting point of 163 ° C. (from acetonitrile) are analogously to Example 5 from 2.2 g of 5-trifluoromethyl-2-mercaptobenzimidazole and 2, 2 9 2-chloromethyl-4-methoxy-3,5-dimethylpyridine - Get hydrochloride.
- reaction of 2-hydroxymethyl-4-methoxy-3-methylpyridine or 2-hydroxymethyl-4-methoxy-3,5-dimethylpyridine with thionyl chloride gives 2-chloromethyl-4-methoxy-3-methylpyridine hydrochloride ( Mp 151-153 ° C, from isopropanol / ether) or 2-chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride (mp. 128 0 C, from isopropanol / ether).
- the compounds 2-hydroxymethyl-4-methoxypyridine and 2-hydroxymethyl-4-methoxy-3-methylpyridine are based on or according to the instructions of OE Schulz and S.Fedders, Arch. Pharm.
- a suspension of 20.0 g (0.092 mol) of 5-trifluoromethyl-2-mercaptobenzimidazole and 13.1 g (0.092 mol) of methyl iodide in 200 ml of ethanol is boiled under reflux for 3 hours. After the solvent has been stripped off in vacuo, the residue is recrystallized from acetonitrile. 17.5 g (82%) of 5-trifluoromethyl-2-methylthiobenzimidazole, mp. 145-146 ° C., are obtained. 3 g (0.013 mol) of this are suspended in 50 ml of methylene chloride.
- the substituted benzimidazoles of the general formula I and their salts have valuable pharmacological properties which make them commercially usable. They clearly inhibit gastric acid secretion from warm-blooded animals and also have an excellent gastric and intestinal protective effect in warm-blooded animals. This gastric and intestinal protective effect is already observed when doses are administered which are below the acid secretion-inhibiting doses.
- stomach and intestinal protection means the prevention and treatment of gastrointestinal diseases, in particular gastrointestinal inflammatory diseases and lesions (such as, for example, ulcer ventriculi, duodenal ulcer, gastritis, hyperacid or drug-induced irritable stomach), which are caused, for example, by microorganisms, bacterial toxins, Medications (e.g. certain anti-inflammatory drugs and anti-rheumatic drugs), chemicals (e.g. ethanol), stomach acid or stressful situations can be caused.
- gastrointestinal inflammatory diseases and lesions such as, for example, ulcer ventriculi, duodenal ulcer, gastritis, hyperacid or drug-induced irritable stomach
- Medications e.g. certain anti-inflammatory drugs and anti-rheumatic drugs
- chemicals e.g. ethanol
- Another advantage of the compounds according to the invention is their comparatively high chemical stability.
- the compounds according to the invention surprisingly prove to be clearly superior to the compounds known from the prior art. Because of these properties, the substituted benzimidazoles and their pharmacologically acceptable salts are outstandingly suitable for use in human and veterinary medicine, and they are used in particular for the treatment and prophylaxis of diseases of the stomach and intestines and those diseases which are based on excessive gastric acid secretion .
- the invention therefore furthermore relates to the compounds according to the invention for use in the treatment and prophylaxis of the abovementioned diseases.
- the invention also includes the use of the compounds according to the invention in the production of medicaments which are used for the treatment and prophylaxis of the abovementioned diseases.
- the invention further relates to medicaments which contain one or more substituted benzimidazoles of the general formula I and / or their pharmacologically tolerable salts.
- the pharmaceuticals are produced by methods known per se and familiar to the person skilled in the art.
- auxiliaries which are suitable for the desired pharmaceutical formulations on the basis of his specialist knowledge.
- solvents for example antioxidants, dispersants, emulsifiers, defoamers, taste correctives, preservatives, solubilizers or colorants can be used.
- the active compounds can be administered orally or parenterally, with oral and intravenous administration being preferred.
- the active ingredient (s) when administered orally in a daily dose of about 0.01 to about 20, preferably 0.05 to 7, in particular 0.1 to 2 mg / kg body weight in the form of several, preferably 1 to 4 individual doses to achieve the desired result.
- similar or generally lower doses in particular when the active compounds are administered intravenously
- the determination of the respectively required Optimal dosage and type of application of the active ingredients can easily be done by any specialist on the basis of his specialist knowledge.
- the pharmaceutical preparations can also contain one or more pharmacologically active constituents of other groups of medicaments, such as antacids, for example aluminum hydroxide, magnesium aluminate; Tranquilizers, such as benzodiazepines, for example diazepam; Antispasmodics, e.g. Bietamiverin, Camylofin; Anticholinergics, e.g. Oxyphencyclimine, phencarbamide; Lökalanaesthetics, such as Tetracaine, procaine; optionally also contain ferments, vitamins or amino acids.
- antacids for example aluminum hydroxide, magnesium aluminate
- Tranquilizers such as benzodiazepines, for example diazepam
- Antispasmodics e.g. Bietamiverin, Camylofin
- Anticholinergics e.g. Oxyphencyclimine, phencarbamide
- Lökalanaesthetics
- the excellent gastric protective effect and the gastric secretion-inhibiting effect of the substituted benzimidazoles according to the invention can be demonstrated in animal experiments using the Shay rat model.
- the compounds according to the invention are several times superior to the prior art with regard to the gastric protective effect and the gastric secretion-inhibiting effect.
- the compounds examined were numbered as follows: The influence of the compounds according to the invention on gastric lesion formation triggered by pylorus ligation (4 h; so-called Shay rat) and oral administration of 100 mg / kg acetylsalicylic acid and gastric secretion (HC1) during 4 h in the rat is shown in the following table.
- the ED 25 and E050 denote those doses that reduce the mean lesion index or HCI secretion by 25% and 50% compared to the control.
- the dose tolerata of all tested compounds is above 1000 mg / kg [p.o.] in the mouse.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH708181 | 1981-11-05 | ||
CH708081 | 1981-11-05 | ||
CH7080/81 | 1981-11-05 | ||
CH7081/81 | 1981-11-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0080602A1 true EP0080602A1 (de) | 1983-06-08 |
Family
ID=25700722
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP82110054A Withdrawn EP0080602A1 (de) | 1981-11-05 | 1982-10-30 | Substituierte Benzimidazole, Verfahren zu ihrer Herstellung, ihre Anwendung und sie enthaltende Arzneimittel |
Country Status (11)
Country | Link |
---|---|
US (1) | US4472409A (no) |
EP (1) | EP0080602A1 (no) |
AU (1) | AU544288B2 (no) |
DE (1) | DE3240248A1 (no) |
DK (1) | DK491682A (no) |
ES (2) | ES8604199A1 (no) |
FI (1) | FI823787L (no) |
GR (1) | GR77370B (no) |
HU (1) | HU187521B (no) |
NO (1) | NO823691L (no) |
PT (1) | PT75805B (no) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2126226A (en) * | 1982-08-26 | 1984-03-21 | Haessle Ab | Pyridine derivatives |
EP0130729A2 (en) * | 1983-07-01 | 1985-01-09 | The Upjohn Company | Alkylthio- and alkylsulfinyl-benzimidazole derivatives |
EP0150586A2 (en) * | 1983-12-05 | 1985-08-07 | The Upjohn Company | 2-(Pyridylmethylthio)benzimidazoles and 2-(pyridylmethylsulfinyl)benzimidazoles |
FR2567123A1 (fr) * | 1984-07-06 | 1986-01-10 | Fisons Ltd | Nouveaux composes polycycliques heterocycliques derives du benzimidazole, du benzoxazole ou du benzothiazole, procede et intermediaire pour leur preparation ainsi que leur utilisation pharmaceutique, en particulier pour le traitement d'affections gastriques |
EP0173664A2 (en) * | 1984-08-10 | 1986-03-05 | Aktiebolaget Hässle | Biologically active benzimidazole compounds and process for their preparation |
EP0174726A1 (en) * | 1984-08-16 | 1986-03-19 | Takeda Chemical Industries, Ltd. | Pyridine derivatives and their production |
EP0074341B1 (en) * | 1981-08-13 | 1986-03-26 | Aktiebolaget Hässle | Novel pharmaceutical compositions |
WO1986002646A1 (en) * | 1984-10-31 | 1986-05-09 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft M | New picoline derivatives, preparation process thereof, utilization thereof and drugs containing them |
FR2576900A1 (fr) * | 1985-02-06 | 1986-08-08 | Kotobuki Seiyaku Co Ltd | Derives de cyclohepto-imidazole 2-substitue, agents anti-ulcereux et procede pour leur preparation |
EP0194458A1 (en) * | 1985-02-12 | 1986-09-17 | Banyu Pharmaceutical Co., Ltd. | New indole derivatives, the production and uses thereof |
US4689331A (en) * | 1984-11-08 | 1987-08-25 | Aktiebolaget Hassle | Substituted 2-pyridinyl benzimidazoles, and their use for inhibiting gastric acid secretion |
EP0237200A2 (en) * | 1986-02-13 | 1987-09-16 | Takeda Chemical Industries, Ltd. | Use of basic inorganic salts of magnesium or calcium for the stabilisation of benzimidazole derivatives |
EP0244380A2 (en) * | 1986-04-30 | 1987-11-04 | Aktiebolaget Hässle | Pharmaceutical formulations of acid labile substances for oral use |
EP0247983A2 (en) * | 1986-04-30 | 1987-12-02 | Aktiebolaget Hässle | New pharmaceutical preparation for oral use |
EP0302720A1 (en) * | 1987-08-04 | 1989-02-08 | Takeda Chemical Industries, Ltd. | Production of 2-(2-Pyridylmethylsulfinyl)-benzimidazole compounds |
US5433959A (en) * | 1986-02-13 | 1995-07-18 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
US6749864B2 (en) | 1986-02-13 | 2004-06-15 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
WO2006030936A1 (ja) | 2004-09-13 | 2006-03-23 | Takeda Pharmaceutical Company Limited | 酸化化合物の製造方法及び製造装置 |
US8968776B2 (en) | 2004-07-29 | 2015-03-03 | Ucb, Inc. | Composition comprising a benzimidazole and process for its manufacture |
Families Citing this family (62)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
SE8301182D0 (sv) * | 1983-03-04 | 1983-03-04 | Haessle Ab | Novel compounds |
HU191756B (en) * | 1983-05-03 | 1987-04-28 | Byk Gulden Lomberg Chem Fab | Process for preparing new fluoro-alkoxy-benzimidazole derivatives |
DE3333314A1 (de) * | 1983-09-15 | 1985-03-28 | Hoechst Ag, 6230 Frankfurt | Substituierte pyrido(1,2-c)imidazo(1,2-a)benzimidazole, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
ZW4585A1 (en) * | 1984-04-19 | 1985-11-20 | Hoffmann La Roche | Imidazole derivatives |
IL75400A (en) * | 1984-06-16 | 1988-10-31 | Byk Gulden Lomberg Chem Fab | Dialkoxypyridine methyl(sulfinyl or sulfonyl)benzimidazoles,processes for the preparation thereof and pharmaceutical compositions containing the same |
JPS6150979A (ja) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
EP0204215B1 (en) | 1985-05-24 | 1993-08-11 | G.D. Searle & Co. | 2-[(1H-benzimidazol-2-ylsulfinyl)methyl]-benzenamines |
US5869513A (en) * | 1985-05-24 | 1999-02-09 | G. D. Searle & Co. | 2- (1H-benzimidazol-2-ylsulfinyl)methyl!benzenamines |
US4738975A (en) * | 1985-07-02 | 1988-04-19 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, and use as anti-ulcer agents |
DK337086A (da) * | 1985-08-12 | 1987-02-13 | Hoffmann La Roche | Benzimidazolderivater |
AR243167A1 (es) | 1985-08-24 | 1993-07-30 | Hoechst Ag | Procedimiento para la preparacion de toluidinas sustituidas. |
DE3777855D1 (de) | 1986-02-20 | 1992-05-07 | Hoechst Ag | Substituierte thienoimidazol-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer. |
JPS62201884A (ja) * | 1986-02-28 | 1987-09-05 | Tokyo Tanabe Co Ltd | ベンズイミダゾール誘導体及びその製造法 |
WO1987005296A1 (en) * | 1986-03-07 | 1987-09-11 | Pfizer Inc. | 2-[(2-pyridyl)methylsulfinyl]thienoimidazoles and related compounds as antiulcer agents |
US4772619A (en) * | 1986-07-17 | 1988-09-20 | G. D. Searle & Co. | [(1H-benzimidazol-2-ylsulfinyl)methyl]-2-pyridinamines |
US4687775A (en) * | 1986-07-17 | 1987-08-18 | G. D. Searle & Co. | 2-[(Imidazo[1,2-a]pyridinylmethyl)sulfinyl]-1H-benzimidazoles |
US4721718A (en) * | 1986-08-18 | 1988-01-26 | G. D. Searle & Co. | 2-[(imidazo[1,2-a]pyridin-3-ylmethyl)sulfinyl]-1H-benzimidazoles useful in the treatment and prevention of ulcers |
DE3639926A1 (de) * | 1986-11-22 | 1988-06-01 | Hoechst Ag | Substituierte thienoimidazoltoluidin-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer |
DE3723327A1 (de) * | 1987-07-15 | 1989-02-02 | Hoechst Ag | Substituierte thienoimidazol-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer, magenschutzmittel sowie als medikament gegen intestinale entzuendungen |
WO1989003830A1 (en) * | 1987-10-30 | 1989-05-05 | Aktiebolaget Hässle | 2-pyridinylmethyl (sulfinyl or thio)benzimidazoles for treatment of diseases related to bone loss |
AU617721B2 (en) * | 1987-10-30 | 1991-12-05 | Aktiebolaget Hassle | 2-pyridinylmethyl (sulfinyl or thio) benzimidazoles for treatment of diseases related to bone loss |
US5223515A (en) * | 1988-08-18 | 1993-06-29 | Takeda Chemical Industries, Ltd. | Injectable solution containing a pyridyl methylsulfinylbenzimidazole |
AT391693B (de) * | 1988-11-15 | 1990-11-12 | Cl Pharma | Verfahren zur herstellung von 3-5-dimethyl-4methoxypyridinderivaten sowie neues zwischenprodukt hierfuer |
HU203736B (en) * | 1989-04-06 | 1991-09-30 | Gyogyszerkutato Intezet | Process for producing new thiouracil-derivatives and pharmaceutical compositions containing them |
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US4045564A (en) * | 1974-02-18 | 1977-08-30 | Ab Hassle | Benzimidazole derivatives useful as gastric acid secretion inhibitors |
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- 1982-10-29 US US06/437,883 patent/US4472409A/en not_active Expired - Fee Related
- 1982-10-30 EP EP82110054A patent/EP0080602A1/de not_active Withdrawn
- 1982-10-30 DE DE19823240248 patent/DE3240248A1/de not_active Withdrawn
- 1982-11-04 FI FI823787A patent/FI823787L/fi not_active Application Discontinuation
- 1982-11-04 GR GR69728A patent/GR77370B/el unknown
- 1982-11-05 HU HU823570A patent/HU187521B/hu unknown
- 1982-11-05 NO NO82823691A patent/NO823691L/no unknown
- 1982-11-05 PT PT75805A patent/PT75805B/pt unknown
- 1982-11-05 AU AU90195/82A patent/AU544288B2/en not_active Withdrawn - After Issue
- 1982-11-05 ES ES517167A patent/ES8604199A1/es not_active Expired
- 1982-11-05 DK DK491682A patent/DK491682A/da not_active Application Discontinuation
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EP0005129B1 (en) * | 1978-04-14 | 1981-04-29 | Aktiebolaget Hässle | Substituted pyridylsulfinylbenzimidazoles having gastric acid secretion properties, pharmaceutical preparations containing same, and intermediates for their preparation |
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Cited By (50)
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EP0074341B1 (en) * | 1981-08-13 | 1986-03-26 | Aktiebolaget Hässle | Novel pharmaceutical compositions |
US4544750A (en) * | 1982-08-26 | 1985-10-01 | Aktiebolaget Hassle | Certain pyridyl-N-oxide intermediates for the preparation of omeprazole |
GB2126226A (en) * | 1982-08-26 | 1984-03-21 | Haessle Ab | Pyridine derivatives |
US4620008A (en) * | 1982-08-26 | 1986-10-28 | Aktiebolaget Hassle | Processes for the preparation of omeprazole and intermediates therefore |
EP0130729A3 (en) * | 1983-07-01 | 1986-08-06 | The Upjohn Company | Alkylthio- and alkylsulfinyl-benzimidazole derivatives |
EP0130729A2 (en) * | 1983-07-01 | 1985-01-09 | The Upjohn Company | Alkylthio- and alkylsulfinyl-benzimidazole derivatives |
EP0150586A2 (en) * | 1983-12-05 | 1985-08-07 | The Upjohn Company | 2-(Pyridylmethylthio)benzimidazoles and 2-(pyridylmethylsulfinyl)benzimidazoles |
EP0150586A3 (en) * | 1983-12-05 | 1985-08-28 | The Upjohn Company | 2-(pyridylmethylthio)benzimidazoles and 2-(pyridylmethylsulfinyl)benzimidazoles |
EP0174717A1 (en) * | 1984-07-06 | 1986-03-19 | FISONS plc | Benzimidazoles, and their production formulation and use as gastric acid secretion inhibitors |
FR2567123A1 (fr) * | 1984-07-06 | 1986-01-10 | Fisons Ltd | Nouveaux composes polycycliques heterocycliques derives du benzimidazole, du benzoxazole ou du benzothiazole, procede et intermediaire pour leur preparation ainsi que leur utilisation pharmaceutique, en particulier pour le traitement d'affections gastriques |
EP0173664A2 (en) * | 1984-08-10 | 1986-03-05 | Aktiebolaget Hässle | Biologically active benzimidazole compounds and process for their preparation |
EP0173664A3 (en) * | 1984-08-10 | 1986-04-16 | Aktiebolaget Hässle | Biologically active benzimidazole compounds and process for their preparation |
EP0174726A1 (en) * | 1984-08-16 | 1986-03-19 | Takeda Chemical Industries, Ltd. | Pyridine derivatives and their production |
WO1986002646A1 (en) * | 1984-10-31 | 1986-05-09 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft M | New picoline derivatives, preparation process thereof, utilization thereof and drugs containing them |
US4689331A (en) * | 1984-11-08 | 1987-08-25 | Aktiebolaget Hassle | Substituted 2-pyridinyl benzimidazoles, and their use for inhibiting gastric acid secretion |
EP0181846B1 (en) * | 1984-11-08 | 1989-08-02 | Aktiebolaget Hässle | New substituted benzimidazoles, a process for their preparation and their use for inhibiting gastric acid secretion |
FR2576900A1 (fr) * | 1985-02-06 | 1986-08-08 | Kotobuki Seiyaku Co Ltd | Derives de cyclohepto-imidazole 2-substitue, agents anti-ulcereux et procede pour leur preparation |
EP0194458A1 (en) * | 1985-02-12 | 1986-09-17 | Banyu Pharmaceutical Co., Ltd. | New indole derivatives, the production and uses thereof |
EP0423748A1 (en) * | 1986-02-13 | 1991-04-24 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition and its production |
US5879708A (en) * | 1986-02-13 | 1999-03-09 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
EP0237200A3 (en) * | 1986-02-13 | 1988-02-03 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition comprising a benzimidazole compound, its production and its use as an antiulcer agent |
US6749864B2 (en) | 1986-02-13 | 2004-06-15 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
US6521256B2 (en) | 1986-02-13 | 2003-02-18 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
US6380234B1 (en) | 1986-02-13 | 2002-04-30 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition and its production |
US6296875B1 (en) | 1986-02-13 | 2001-10-02 | Takeda Chemical Industries, Ltd. | Method for producing a granule |
EP0237200A2 (en) * | 1986-02-13 | 1987-09-16 | Takeda Chemical Industries, Ltd. | Use of basic inorganic salts of magnesium or calcium for the stabilisation of benzimidazole derivatives |
US5045321A (en) * | 1986-02-13 | 1991-09-03 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition and its production |
EP0446961A2 (en) * | 1986-02-13 | 1991-09-18 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition and its production |
US5093132A (en) * | 1986-02-13 | 1992-03-03 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition and its production |
EP0446961A3 (en) * | 1986-02-13 | 1992-04-01 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition and its production |
US6123962A (en) * | 1986-02-13 | 2000-09-26 | Takeda Chemical Industries, Inc. | Process for producing stabilized pharmaceutical composition |
US6017560A (en) * | 1986-02-13 | 2000-01-25 | Takeda Chemical Industries, Ltd. | Process for producing stabilized pharmaceutical composition |
US5639478A (en) * | 1986-02-13 | 1997-06-17 | Takeda Chemical Industries, Ltd. | Method to stabilize a pharmaceutical composition and its production |
US5433959A (en) * | 1986-02-13 | 1995-07-18 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
EP0247983A3 (en) * | 1986-04-30 | 1988-10-19 | Aktiebolaget Hassle | New pharmaceutical preparation for oral use |
EP0247983A2 (en) * | 1986-04-30 | 1987-12-02 | Aktiebolaget Hässle | New pharmaceutical preparation for oral use |
EP0565210A3 (no) * | 1986-04-30 | 1995-06-07 | Haessle Ab | |
EP0565210A2 (en) * | 1986-04-30 | 1993-10-13 | Aktiebolaget Hässle | Vehicles for oral adminstration of pharmaceutically active acide labile substances |
EP0496437A2 (en) * | 1986-04-30 | 1992-07-29 | Aktiebolaget Hässle | Use of specific core material and layers to obtain pharmaceutical formulations stable to discolouration of omeprazole |
EP0502556A1 (en) * | 1986-04-30 | 1992-09-09 | Aktiebolaget Hässle | Use of specific core material and layers to obtain pharmaceutical formulations stable to discolouration of acid labile compounds |
EP0567201A3 (en) * | 1986-04-30 | 1995-06-07 | Haessle Ab | Vehicle for oral administration of acid labile pharmaceuticals. |
EP0496437A3 (en) * | 1986-04-30 | 1992-09-02 | Aktiebolaget Haessle | Use of specific core material and layers to obtain pharmaceutical formulations stable to discolouration of omeprazole |
EP0567201A2 (en) * | 1986-04-30 | 1993-10-27 | Aktiebolaget Hässle | Vehicles for oral administration of a specific pharmaceutically active acid labile substance |
EP0244380A2 (en) * | 1986-04-30 | 1987-11-04 | Aktiebolaget Hässle | Pharmaceutical formulations of acid labile substances for oral use |
EP0244380A3 (en) * | 1986-04-30 | 1988-10-19 | Aktiebolaget Hassle | Pharmaceutical formulations of acid labile substances for oral use |
EP0302720A1 (en) * | 1987-08-04 | 1989-02-08 | Takeda Chemical Industries, Ltd. | Production of 2-(2-Pyridylmethylsulfinyl)-benzimidazole compounds |
US5578732A (en) * | 1987-08-04 | 1996-11-26 | Takeda Chemical Industries, Ltd. | Production of 2-(2-pyridylmethylsulfinyl) benzimidazole compounds by selective oxidation in the presence of a vanadium catalyst |
US8968776B2 (en) | 2004-07-29 | 2015-03-03 | Ucb, Inc. | Composition comprising a benzimidazole and process for its manufacture |
WO2006030936A1 (ja) | 2004-09-13 | 2006-03-23 | Takeda Pharmaceutical Company Limited | 酸化化合物の製造方法及び製造装置 |
EP2264025A1 (en) | 2004-09-13 | 2010-12-22 | Takeda Pharmaceutical Company Limited | Method to produce a crystalline form of compounds (II') |
Also Published As
Publication number | Publication date |
---|---|
FI823787A0 (fi) | 1982-11-04 |
PT75805B (en) | 1989-07-03 |
ES8604199A1 (es) | 1986-02-01 |
HU187521B (en) | 1986-01-28 |
ES517167A0 (es) | 1986-02-01 |
ES526899A0 (es) | 1985-05-01 |
DK491682A (da) | 1983-05-06 |
GR77370B (no) | 1984-09-11 |
AU544288B2 (en) | 1985-05-23 |
ES8504140A1 (es) | 1985-05-01 |
FI823787L (fi) | 1983-05-06 |
NO823691L (no) | 1983-05-06 |
AU9019582A (en) | 1983-05-12 |
DE3240248A1 (de) | 1983-06-01 |
US4472409A (en) | 1984-09-18 |
PT75805A (en) | 1982-12-01 |
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